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4 Things He Thinks the First Time You Sleep With Him

After my divorce, I had a pretty crazy rebound period that’s run the gamut from horrible to hopeful. While I didn’t think I’d ever be back out there searching for love again, I’ve learned a lot about relationships, and I hope I can pass some of that knowledge on to you. I’m here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamourmag #jake or via email smittenbloggers@gmail.com.

So the Egg Lady and I did it. (And, yes, that’s become her code name. You’ll remember she’s the one who told me on our first date that she’d frozen her eggs.) We had sex on our fourth date, and it was good, great even. The self-assuredness that had first attracted me to her spilled over into the bedroom; she knew what she wanted. Everyone (all two of us) climaxed, and we snuggled in the afterglow. Then: Eyes closed, her arm across my chest, she gave me a thumbs-up and murmured four confusing words, “Well, I needed that.” It was gratifying but puzzling. Was this just a roll in the hay or something more? It was weird to be so physically close and so psychically not. Ironically, these are the kinds of doubts my female friends say they have after their first time with a guy. Well, I may not be able to read Egg Lady’s mind, but I can fill you in on what guys think when we get lucky enough to be naked with you.

We’re Psyched...But Worried You’ll Think It Means Too Much Breaking: Guys like sex. Especially first-time sex with someone we’re actually dating. It makes us happy. Afterward we tend to think very simple, basic thoughts like, I wonder how soon it will be before I get to enjoy that again?What that means for you: Hopefully you’re psyched too! And maybe just leave it at that? The morning after is not the time to have “the talk.” It’s probably a better time to have “morning sex.”

We Stress About Our Performance And that worry tends to, ah, harm our performance by hastening it, if you know what I mean. Sometimes we can't control our excitement about new, gorgeous you. And if we think we’ve failed in pleasing you, we think we’ve failed as men.What that means for you: Have a heart if the sex isn’t good. I bet he’ll improve once he relaxes a bit. However, if the sex was bad because he was only interested in pleasing himself, show that guy the door.

We’re Not Grading You Believe it or not, men do not go into sexual experiences expecting them to be like the last porn we watched. We know what’s real and what’s not, and when we’re in bed with an actual naked female, the last thing on our mind is some other naked female, particularly one with fake hair, fake body parts, and fake moans.What that means for you: Cliche alert— be yourself. There’s no need for theatrics, acrobatics, or special lighting, unless those are your thing. We’re there for you.

We Don’t Read a Lot Into It Ultimately, the first time is...the first time, not necessarily a blueprint for all future sex-capades. I dated a woman after college, and we had incredible first sex: tender, sweaty, and mind-blowing. But our relationship didn’t work, and the sex was never that good again. Likewise, bad sex the first time isn’t going to send us running for the hills. Remember, we’re psyched just to be there. What that means for you: Takes a lot of the pressure off, right? Honestly, I’m on the fence about whether Egg Lady and I truly connect, and I think she is too. We need to spend more time together—in bed and out—so that’s the plan. I’ll let you know how it goes.

—Jake For more advice, download Glamour's digital edition, or pick up an issue on newsstands now. P.S. Do you have dating or relationship questions for Jake? Ask in the comments below, tweet him @glamourmag with #jake, or email smittenbloggers@gmail.com.